#------------------------------------------------------------------------------
#$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/02/57/4025740.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_4025740
loop_
_publ_author_name
'Daniel J. Kerr'
'Jonathan M. White'
'Bernard L. Flynn'
_publ_section_title
;
 A Reductive-Coupling plus Nazarov Cyclization Sequence in the Asymmetric
 Synthesis of Five-Membered Carbocycles
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              7073
_journal_page_last               7084
_journal_paper_doi               10.1021/jo100736p
_journal_volume                  75
_journal_year                    2010
_chemical_formula_sum            'C20 H23 N O4'
_chemical_formula_weight         341.39
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.793(2)
_cell_length_b                   13.870(3)
_cell_length_c                   16.681(5)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      30
_cell_measurement_theta_min      15
_cell_volume                     1803.0(8)
_computing_cell_refinement       'CAD4 Express (Enraf Nonius, 1994)'
_computing_data_collection       'CAD4 Express (Enraf Nonius, 1994)'
_computing_data_reduction        'XCAD4 (Harms & Wocadlo, 1995)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Enraf Nonius CAD4'
_diffrn_measurement_method       'non-profiled omega/2theta scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54180
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0235
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            1971
_diffrn_reflns_theta_full        69.93
_diffrn_reflns_theta_max         69.93
_diffrn_reflns_theta_min         4.15
_diffrn_standards_decay_%        1.5
_diffrn_standards_interval_time  3600
_diffrn_standards_number         25
_exptl_absorpt_coefficient_mu    0.710
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.258
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             728
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.236
_refine_diff_density_min         -0.216
_refine_diff_density_rms         0.056
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.1(4)
_refine_ls_extinction_coef       0.0194(15)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     230
_refine_ls_number_reflns         1971
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.072
_refine_ls_R_factor_all          0.0548
_refine_ls_R_factor_gt           0.0467
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0792P)²+0.1472P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1160
_refine_ls_wR_factor_ref         0.1238
_reflns_number_gt                1718
_reflns_number_total             1971
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo100736p_si_001.cif
_cod_data_source_block           jmwbf2
_cod_database_code               4025740
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C -0.0425(3) 0.68628(17) 0.08688(15) 0.0425(6) Uani 1 1 d . . .
C2 C 0.0686(4) 0.6851(2) 0.15157(18) 0.0587(7) Uani 1 1 d . . .
H2 H 0.0598 0.7322 0.1910 0.070 Uiso 1 1 calc R . .
C3 C 0.1928(5) 0.6140(3) 0.1577(2) 0.0731(10) Uani 1 1 d . . .
H3 H 0.2674 0.6136 0.2012 0.088 Uiso 1 1 calc R . .
C4 C 0.2060(5) 0.5442(2) 0.0998(3) 0.0741(10) Uani 1 1 d . . .
H4 H 0.2904 0.4970 0.1038 0.089 Uiso 1 1 calc R . .
C5 C 0.0950(5) 0.5439(2) 0.0361(3) 0.0725(10) Uani 1 1 d . . .
H5 H 0.1026 0.4961 -0.0028 0.087 Uiso 1 1 calc R . .
C6 C -0.0288(4) 0.61548(19) 0.03001(18) 0.0545(7) Uani 1 1 d . . .
H6 H -0.1037 0.6153 -0.0134 0.065 Uiso 1 1 calc R . .
C7 C -0.1839(3) 0.76119(17) 0.07859(15) 0.0415(6) Uani 1 1 d . . .
H7 H -0.1998 0.7774 0.0219 0.050 Uiso 1 1 calc R . .
C8 C -0.3542(4) 0.7281(2) 0.11415(17) 0.0528(7) Uani 1 1 d . . .
H8A H -0.4424 0.7265 0.0732 0.063 Uiso 1 1 calc R . .
H8B H -0.3429 0.6640 0.1368 0.063 Uiso 1 1 calc R . .
C9 C -0.2808(4) 0.8657(3) 0.1807(2) 0.0652(9) Uani 1 1 d . . .
C10 C -0.0150(3) 0.90974(17) 0.10438(15) 0.0436(6) Uani 1 1 d . . .
C11 C 0.0276(3) 0.99511(17) 0.15553(17) 0.0478(6) Uani 1 1 d . . .
H11 H -0.0365 0.9914 0.2060 0.057 Uiso 1 1 calc R . .
C12 C -0.0195(4) 1.0888(2) 0.11122(19) 0.0546(7) Uani 1 1 d . . .
C13 C 0.1300(4) 1.1519(2) 0.11151(18) 0.0561(7) Uani 1 1 d . . .
C14 C 0.2634(4) 1.1059(2) 0.14348(18) 0.0535(7) Uani 1 1 d . . .
C15 C 0.2210(3) 1.0059(2) 0.17359(18) 0.0508(7) Uani 1 1 d . . .
H15 H 0.2847 0.9585 0.1417 0.061 Uiso 1 1 calc R . .
C16 C 0.2655(4) 0.9919(2) 0.26191(18) 0.0577(7) Uani 1 1 d . . .
H16A H 0.3846 1.0098 0.2699 0.069 Uiso 1 1 calc R . .
H16B H 0.1959 1.0357 0.2935 0.069 Uiso 1 1 calc R . .
C17 C 0.2397(5) 0.8909(2) 0.2936(2) 0.0689(9) Uani 1 1 d . . .
H17A H 0.3011 0.8459 0.2595 0.083 Uiso 1 1 calc R . .
H17B H 0.1187 0.8748 0.2910 0.083 Uiso 1 1 calc R . .
C18 C 0.3016(6) 0.8792(3) 0.3792(2) 0.0889(12) Uani 1 1 d . . .
H18A H 0.4224 0.8925 0.3818 0.133 Uiso 1 1 calc R . .
H18B H 0.2808 0.8143 0.3967 0.133 Uiso 1 1 calc R . .
H18C H 0.2409 0.9233 0.4133 0.133 Uiso 1 1 calc R . .
C19 C 0.4428(4) 1.1440(3) 0.1504(2) 0.0761(10) Uani 1 1 d . . .
H19A H 0.4657 1.1869 0.1066 0.114 Uiso 1 1 calc R . .
H19B H 0.5226 1.0912 0.1490 0.114 Uiso 1 1 calc R . .
H19C H 0.4551 1.1781 0.2002 0.114 Uiso 1 1 calc R . .
C20 C 0.1254(6) 1.2519(2) 0.0771(3) 0.0774(10) Uani 1 1 d . . .
H20A H 0.1143 1.2979 0.1197 0.116 Uiso 1 1 calc R . .
H20B H 0.0293 1.2577 0.0414 0.116 Uiso 1 1 calc R . .
H20C H 0.2297 1.2639 0.0481 0.116 Uiso 1 1 calc R . .
N1 N -0.1528(3) 0.84934(15) 0.12459(12) 0.0431(5) Uani 1 1 d . . .
O1 O 0.0677(3) 0.88883(15) 0.04564(12) 0.0585(6) Uani 1 1 d . . .
O2 O -0.2931(4) 0.9309(2) 0.2265(2) 0.1185(14) Uani 1 1 d . . .
O3 O -0.3973(3) 0.7958(2) 0.17486(14) 0.0823(8) Uani 1 1 d . . .
O4 O -0.1591(3) 1.10514(18) 0.08117(19) 0.0833(8) Uani 1 1 d . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 C1 C2 118.9(3) . . ?
C6 C1 C7 118.9(2) . . ?
C2 C1 C7 122.1(2) . . ?
C1 C2 C3 120.2(3) . . ?
C4 C3 C2 120.2(3) . . ?
C5 C4 C3 120.0(3) . . ?
C4 C5 C6 119.6(3) . . ?
C1 C6 C5 121.1(3) . . ?
N1 C7 C1 113.8(2) . . ?
N1 C7 C8 101.1(2) . . ?
C1 C7 C8 112.9(2) . . ?
O3 C8 C7 106.5(2) . . ?
O2 C9 O3 123.1(3) . . ?
O2 C9 N1 128.1(3) . . ?
O3 C9 N1 108.8(2) . . ?
O1 C10 N1 117.4(2) . . ?
O1 C10 C11 122.3(2) . . ?
N1 C10 C11 120.3(2) . . ?
C10 C11 C12 110.0(2) . . ?
C10 C11 C15 113.8(2) . . ?
C12 C11 C15 104.2(2) . . ?
O4 C12 C13 127.1(3) . . ?
O4 C12 C11 124.6(3) . . ?
C13 C12 C11 108.3(2) . . ?
C14 C13 C12 109.8(3) . . ?
C14 C13 C20 127.9(3) . . ?
C12 C13 C20 122.3(3) . . ?
C13 C14 C19 126.2(3) . . ?
C13 C14 C15 113.7(3) . . ?
C19 C14 C15 120.1(3) . . ?
C14 C15 C16 112.8(2) . . ?
C14 C15 C11 103.7(2) . . ?
C16 C15 C11 113.5(2) . . ?
C17 C16 C15 115.2(3) . . ?
C16 C17 C18 112.7(3) . . ?
C9 N1 C10 128.0(2) . . ?
C9 N1 C7 111.8(2) . . ?
C10 N1 C7 119.97(19) . . ?
C9 O3 C8 111.9(2) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C6 1.370(4) . ?
C1 C2 1.384(4) . ?
C1 C7 1.521(3) . ?
C2 C3 1.386(5) . ?
C3 C4 1.371(5) . ?
C4 C5 1.370(5) . ?
C5 C6 1.388(4) . ?
C7 N1 1.464(3) . ?
C7 C8 1.524(4) . ?
C8 O3 1.422(4) . ?
C9 O2 1.187(4) . ?
C9 O3 1.331(4) . ?
C9 N1 1.387(3) . ?
C10 O1 1.208(3) . ?
C10 N1 1.403(3) . ?
C10 C11 1.497(3) . ?
C11 C12 1.540(4) . ?
C11 C15 1.544(4) . ?
C12 O4 1.219(4) . ?
C12 C13 1.457(4) . ?
C13 C14 1.332(4) . ?
C13 C20 1.501(5) . ?
C14 C19 1.499(4) . ?
C14 C15 1.512(4) . ?
C15 C16 1.526(4) . ?
C16 C17 1.510(4) . ?
C17 C18 1.516(5) . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30659291
